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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 3| March 2009| Pages o495-o496
doi:10.1107/S1600536809003870

3-{1-[4-(2-Methyl­prop­yl)phen­yl]eth­yl}-1-(morpholinometh­yl)-4-(4-nitro­benzyl­­idene­amino)-1H-1,2,4-triazole-5(4H)-thione

Hoong-Kun Fun,a* Suchada Chantrapromma,b‡ K. V. Sujithc and B. Kallurayac

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
*Correspondence e-mail: hkfun@usm.my

(Received 30 January 2009; accepted 2 February 2009; online 11 February 2009)

The title ibuprofen-containing Mannich derivative, C26H32N6O3S, crystallizes with two independent mol­ecules in the asymmetric unit. The morpholine ring in each mol­ecule adopts a chair conformation. The 1,2,4-triazole ring forms dihedral angles of 2.13 (10) and 75.52 (10)° with the two substituted benzene rings in one mol­ecule, with corresponding values of 19.36 (11)° and 89.03 (10)° in the other. The nitro groups are twisted from the attached benzene ring in each mol­ecule. In the crystal packing, mol­ecules are linked into supra­molecular chains via weak C—H⋯O, C—H⋯N and C—H⋯S inter­actions, and C—H⋯π and N—O⋯π links also occur.

Related literature

For values of bond lengths, see Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For ring conformations, see Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For related structures see, for example, Fun et al. (2008[Fun, H.-K., Jebas, S. R., Sujith, K. V., Patil, P. S., Kalluraya, B. & Dharmaprakash, S. M. (2008). Acta Cryst. E64, o1001-o1002.]). For background to the activities and applications of Mannich derivatives. see, for example, Ferlin et al. (2002[Ferlin, M. G., Chiarelotto, G., Antonucci, F., Caparrotta, L. & Froldi, G. (2002). Eur. J. Med. Chem. 37, 427-434.]); Holla et al. (2003[Holla, B. S., Veerendra, B., Shivananda, M. K. & Poojary, B. (2003). Eur. J. Med. Chem. 38, 759-767.]); Joshi et al. (2004[Joshi, S., Khosla, N. & Tiwari, P. (2004). Bioorg. Med. Chem. 12, 571-576.]); Karthikeyan et al. (2006[Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482-7489.]); Kawail et al. (2005[Kawail, S., Kojima, F. & Kusunoki, N. (2005). Allergol. Int. 54, 209-215.]); Klasser & Epstein, (2005[Klasser, G. D. & Epstein, J. (2005). J. Can. Dent. Assoc. 71, 575-580.]); Lopes et al. (2004[Lopes, F., Capela, R., Goncaves, J. O., Horton, P. N., Hursthouse, M. B., Iley, J., Casimiro, C. M., Bom, J. & Moreira, R. (2004). Tetrahedron Lett. 45, 7663-7666.]); Malinka et al. (2005[Malinka, W., Swiatek, P., Filipek, B., Sapa, J., Jerierska, A. & Koll, A. (2005). Farmaco, 60, 961-968.]); Raman et al. (2004[Raman, N., Esthar, S. & Thangaraja, C. (2004). J. Chem. Sci. 116, 209-213.]); Tramontini et al. (1988[Tramontini, M., Angiolini, L. & Ghedini, N. (1988). Polymer, 29, 771-788.]).

[Scheme 1]

Experimental

Crystal data

  • C26H32N6O3S

  • Mr = 508.65

  • Triclinic, [P \overline 1]

  • a = 10.3104 (1) Å

  • b = 16.9650 (2) Å

  • c = 17.1863 (2) Å

  • α = 62.656 (1)°

  • β = 79.907 (1)°

  • γ = 78.307 (1)°

  • V = 2603.16 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.16 mm−1

  • T = 100.0 (1) K

  • 0.44 × 0.25 × 0.15 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.931, Tmax = 0.976

  • 50102 measured reflections

  • 15162 independent reflections

  • 11421 reflections with I > 2σ(I)

  • Rint = 0.044
Refinement

  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.161

  • S = 1.05

  • 15162 reflections

  • 655 parameters

  • H-atom parameters constrained

  • Δρmax = 1.23 e Å−3

  • Δρmin = −0.55 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C4A—H4AB⋯O3Ai 0.97 2.53 3.450 (3) 157
C5A—H5AB⋯O3Bii 0.97 2.56 3.221 (3) 126
C8A—H8AA⋯S1A 0.93 2.43 3.186 (2) 138
C13A—H13A⋯O3Aiii 0.93 2.43 3.064 (3) 125
C13B—H13B⋯N1Aiv 0.93 2.55 3.332 (2) 141
C15A—H15A⋯O1Av 0.98 2.27 3.212 (2) 161
C8B—H8BA⋯S1B 0.93 2.55 3.1823 (19) 125
C22B—H22D⋯S1Aiv 0.97 2.86 3.801 (2) 163
N6A—O2A⋯Cg1i 1.23 (1) 3.00 (1) 3.6928 (19) 115 (1)
C11A—H11A⋯Cg2i 0.93 2.52 3.405 (2) 158
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x+1, y, z+1; (iii) -x, -y+1, -z+2; (iv) x-1, y, z-1; (v) x-1, y, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003870/tk2368sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003870/tk2368Isup2.hkl

checkCIF report


Comment top

Non-steroidal anti-inflammatory drugs (NSAIDs) such as ibuprofen are widely used in the treatment of pain and inflammation (Kawail et al., 2005; Klasser & Epstein, 2005). The Mannich reaction is a three-component condensation reaction involving active hydrogen-containing compounds, formaldehyde and a secondary amine (Raman et al., 2004). Mannich bases have been reported as potential biological agents. Thus, they find applications as antitubercular (Joshi et al., 2004), antimalarial (Lopes et al., 2004), vasorelaxing (Ferlin et al., 2002), anticancer (Holla et al., 2003), and analgesic drugs (Malinka et al., 2005). They are also used in the polymer industry as paints and surface active agents (Tramontini et al., 1988). Some Mannich bases are reported to exhibit activity in vitro against murine P388 lymphocytic leukemia cells (Karthikeyan et al., 2006). According to our previous work (Fun et al., 2008), we are interested in the synthesis, biological activities and crystal structures of ibuprofen- containing Mannich derivatives. Prompted by the biological activities of these derivatives, we herein report the synthesis and the crystal structure determination of the title compound, (I).

In the asymmetric unit of (I), Fig. 1, there are two independent molecules, designated A and B. The morpholine ring (C1–C4//N1/O1) in each molecule is in the standard chair conformation (Cremer & Pople, 1975), and is (-)-anti-clinal with respect to the 1,2,4-triazole ring as seen in the torsion angle C6–N2–C5–N1 = -98.3 (2)° in molecule A; -90.8 (2)° in molecule B. The 1,2,4-triazole ring forms dihedral angles of 2.13 (10)° and 75.52 (10)° with the C9–C14 and C16–C21 benzene rings, respectively in molecule A, with corresponding values of 19.36 (11)° and 89.03 (10)° for molecule B. These data indicate the 4-nitrophenyl unit is essentially co-planar with the 1,2,4-triazole ring in molecule A whereas it is twisted in molecule B. In the 4-nitrophenyl unit of each molecule, the nitro group is twisted from the mean plane of the C9–C14 ring as shown by the dihedral angle formed between the mean planes through C12/N6/O2/O3 and C19–C14 ring of 21.63 (11)° in molecule A; the comparable angle is 27.96 (13)° for molecule B. The isobutyl substituent (C22–C25) in each molecule is (-)-syn-clinal with respect to the C16–C21 ring with the torsion angle C18–C19–C22–C23 = -75.7 (2)° in molecule A compared with -74.2 (2)° in molecule B. Bond lengths and angles in molecules A and B are slightly different but all are in normal ranges (Allen et al., 1987) and comparable to those in a related structure (Fun et al., 2008).

In the crystal packing, weak C—H···O interactions (Table 1, Fig. 2) link the molecules into chains along the a-axis. The crystal is further stabilized by weak C—H···O, C—H···π and N—O···π interactions (Table 1); Cg1 and Cg2 are the centroids of N2A–N3A–C7A–N4A–C6A and C16A–C21A rings, respectively.

Related literature top

For values of bond lengths, see Allen et al. (1987). For ring conformations, see Cremer & Pople (1975). For related structures see, for example, Fun et al. (2008). For background to the activities and applications of Mannich derivatives. see, for example, Ferlin et al. (2002); Holla et al. (2003); Joshi et al. (2004); Karthikeyan et al. (2006); Kawail et al. (2005); Klasser & Epstein, (2005); Lopes et al. (2004); Malinka et al. (2005); Raman et al. (2004); Tramontini et al. (1988).

Experimental top

Compound (I) was obtained by the aminomethylation of its corresponding Schiff base, which was obtained by refluxing (3 h) 4-amino-5-[1-(4-isobutylphenyl)ethyl]-4H-1,2,4-triazole-3-thiol (0.01 mol) and 4-nitro benzaldehyde (0.01 mol) in ethanol (50 ml) with the addition of 3 drops of concentrated sulfuric acid. A mixture of the resulting Schiff base (0.01 mol), formaldehyde (40%, 1 ml) and morpholine (0.01 mol) in ethanol (50 ml) was stirred at room temperature for 20 h. The solid product obtained was collected by filtration, washed with ethanol and dried. Yellow block-shaped single crystals were obtained from an ethanol/N,N-dimethylformamide (DMF) (2:1) solution by slow evaporation (Yield 85%, M.p. 387 K).

Refinement top

All H atoms were placed in their calculated positions with d(C—H) = 0.93-0.98 Å, and with Uiso = 1.2-1.5Ueq(C). The rotating group model was used for the methyl groups. The highest residual electron density peak was located 0.86 Å from S1B and the deepest hole was located 0.54 Å from S1B.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are omitted for clarify.
[Figure 2] Fig. 2. A packing diagram for (I), viewed along the c axis, showing supramolecular chains along the a axis. Weak C—H···O interactions are shown as dashed lines.
3-{1-[4-(2-Methylpropyl)phenyl]ethyl}-1-(morpholinomethyl)-4-(4- nitrobenzylideneamino)-1H-1,2,4-triazole-5(4H)-thione top
Crystal data top
C26H32N6O3SZ = 4
Mr = 508.65F(000) = 1080
Triclinic, P1Dx = 1.298 Mg m−3
Hall symbol: -P 1Melting point: 387 K
a = 10.3104 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 16.9650 (2) ÅCell parameters from 15162 reflections
c = 17.1863 (2) Åθ = 1.3–30.0°
α = 62.656 (1)°µ = 0.16 mm−1
β = 79.907 (1)°T = 100 K
γ = 78.307 (1)°Block, yellow
V = 2603.16 (6) Å30.44 × 0.25 × 0.15 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		15162 independent reflections
Radiation source: fine-focus sealed tube11421 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 1.3°
ω scansh = −14→14
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −23→23
Tmin = 0.931, Tmax = 0.976l = −24→24
50102 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.079P)2 + 1.217P]
where P = (Fo2 + 2Fc2)/3
15162 reflections(Δ/σ)max = 0.001
655 parametersΔρmax = 1.23 e Å−3
0 restraintsΔρmin = −0.55 e Å−3
Crystal data top
C26H32N6O3Sγ = 78.307 (1)°
Mr = 508.65V = 2603.16 (6) Å3
Triclinic, P1Z = 4
a = 10.3104 (1) ÅMo Kα radiation
b = 16.9650 (2) ŵ = 0.16 mm−1
c = 17.1863 (2) ÅT = 100 K
α = 62.656 (1)°0.44 × 0.25 × 0.15 mm
β = 79.907 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		15162 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		11421 reflections with I > 2σ(I)
Tmin = 0.931, Tmax = 0.976Rint = 0.044
50102 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.161H-atom parameters constrained
S = 1.05Δρmax = 1.23 e Å−3
15162 reflectionsΔρmin = −0.55 e Å−3
655 parameters
Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.78547 (5)0.25240 (3)1.21421 (3)0.02654 (11)
O1A1.29830 (15)0.18812 (11)1.04587 (11)0.0379 (4)
O2A0.08384 (14)0.68658 (9)1.03927 (10)0.0290 (3)
O3A−0.01242 (15)0.60984 (10)1.00038 (11)0.0378 (4)
N1A1.08560 (15)0.09773 (11)1.15711 (11)0.0242 (3)
N2A0.84566 (15)0.14004 (10)1.13677 (10)0.0208 (3)
N3A0.80185 (15)0.11781 (10)1.07871 (10)0.0215 (3)
N4A0.67012 (14)0.23297 (10)1.09020 (10)0.0195 (3)
N5A0.55767 (15)0.29644 (10)1.07082 (10)0.0211 (3)
N6A0.08197 (15)0.62115 (11)1.02708 (10)0.0243 (3)
C1A1.12567 (19)0.09867 (15)1.07070 (14)0.0300 (4)
H1AA1.07370.14841.02680.036*
H1AB1.11010.04351.07220.036*
C2A1.2725 (2)0.10822 (17)1.04711 (16)0.0355 (5)
H2AA1.32400.05691.08980.043*
H2AB1.30010.10940.98970.043*
C3A1.2609 (2)0.18562 (15)1.13062 (15)0.0311 (4)
H3AA1.28030.23961.12990.037*
H3AB1.31290.13471.17340.037*
C4A1.11489 (19)0.17850 (13)1.15776 (13)0.0257 (4)
H4AA1.09230.17531.21630.031*
H4AB1.06210.23111.11730.031*
C5A0.95186 (18)0.07875 (12)1.19086 (12)0.0241 (4)
H5AA0.93410.07871.24820.029*
H5AB0.94720.01871.19950.029*
C6A0.76712 (17)0.20949 (12)1.14700 (11)0.0200 (3)
C7A0.69639 (17)0.17506 (12)1.05098 (11)0.0200 (3)
C8A0.53313 (18)0.35138 (12)1.10518 (12)0.0226 (3)
H8AA0.59010.34831.14320.027*
C9A0.41469 (17)0.41923 (12)1.08419 (11)0.0206 (3)
C10A0.39129 (18)0.47859 (12)1.12251 (12)0.0225 (3)
H10A0.44920.47281.16120.027*
C11A0.28338 (17)0.54563 (12)1.10365 (12)0.0216 (3)
H11A0.26850.58571.12830.026*
C12A0.19824 (17)0.55113 (12)1.04683 (12)0.0217 (3)
C13A0.21717 (19)0.49364 (13)1.00776 (13)0.0255 (4)
H13A0.15770.49920.97000.031*
C14A0.32678 (18)0.42769 (13)1.02631 (12)0.0241 (4)
H14A0.34210.38881.00020.029*
C15A0.61192 (17)0.17984 (12)0.98601 (12)0.0215 (3)
H15A0.51880.19541.00460.026*
C16A0.64620 (17)0.25239 (12)0.89457 (12)0.0209 (3)
C17A0.54930 (17)0.32166 (14)0.84976 (13)0.0247 (4)
H17A0.46320.32490.87680.030*
C18A0.57976 (18)0.38588 (13)0.76534 (13)0.0250 (4)
H18A0.51360.43180.73660.030*
C19A0.70763 (18)0.38326 (13)0.72233 (12)0.0234 (4)
C20A0.80489 (18)0.31444 (13)0.76766 (12)0.0241 (4)
H20A0.89110.31170.74080.029*
C21A0.77525 (17)0.24982 (13)0.85243 (12)0.0225 (3)
H21A0.84170.20440.88150.027*
C22A0.7373 (2)0.45101 (14)0.62909 (13)0.0306 (4)
H22A0.83280.45060.61630.037*
H22B0.69770.51020.62320.037*
C23A0.6842 (2)0.43256 (16)0.56158 (14)0.0347 (5)
H23A0.58790.43280.57570.042*
C24A0.7086 (3)0.5073 (2)0.46935 (16)0.0527 (7)
H24A0.67230.49640.42790.079*
H24B0.80260.50860.45410.079*
H24C0.66630.56370.46790.079*
C25A0.7450 (3)0.34170 (18)0.56554 (16)0.0419 (5)
H25A0.70980.33270.52260.063*
H25B0.72380.29560.62320.063*
H25C0.83980.33930.55340.063*
C26A0.6264 (2)0.08819 (14)0.98539 (14)0.0299 (4)
H26A0.59890.04441.04290.045*
H26B0.71770.07060.96930.045*
H26C0.57170.09230.94350.045*
S1B0.41995 (5)−0.06478 (3)0.71988 (3)0.02460 (10)
O1B0.15427 (15)0.26352 (11)0.76303 (12)0.0394 (4)
O2B−0.0664 (2)−0.15572 (14)0.39243 (12)0.0545 (5)
O3B0.09808 (18)−0.12340 (11)0.28982 (11)0.0414 (4)
N1B0.39755 (15)0.14654 (11)0.76939 (11)0.0239 (3)
N2B0.49615 (14)0.10079 (10)0.65296 (10)0.0204 (3)
N3B0.51644 (15)0.17613 (10)0.57463 (10)0.0212 (3)
N4B0.42374 (14)0.08104 (10)0.55504 (9)0.0185 (3)
N5B0.36838 (14)0.05378 (10)0.50452 (10)0.0194 (3)
N6B0.0391 (2)−0.12622 (12)0.35983 (12)0.0340 (4)
C1B0.26918 (18)0.12013 (14)0.77168 (13)0.0262 (4)
H1BA0.27210.05590.80690.031*
H1BB0.25260.13430.71250.031*
C2B0.1578 (2)0.16859 (16)0.81025 (16)0.0349 (5)
H2BA0.07350.15270.80850.042*
H2BB0.16990.14970.87130.042*
C3B0.2782 (2)0.28701 (16)0.76481 (17)0.0366 (5)
H3BA0.29410.26760.82530.044*
H3BB0.27460.35170.73440.044*
C4B0.3912 (2)0.24449 (13)0.72165 (14)0.0290 (4)
H4BA0.37690.26450.66070.035*
H4BB0.47440.26200.72290.035*
C5B0.50905 (18)0.09861 (13)0.73837 (12)0.0236 (4)
H5BA0.52090.03660.78220.028*
H5BB0.58860.12370.73290.028*
C6B0.44259 (16)0.03925 (12)0.64404 (12)0.0200 (3)
C7B0.47454 (16)0.16148 (12)0.51579 (12)0.0185 (3)
C8B0.28102 (17)0.00087 (12)0.54485 (12)0.0210 (3)
H8BA0.2578−0.01810.60490.025*
C9B0.21784 (16)−0.02954 (12)0.49513 (12)0.0196 (3)
C10B0.13500 (18)−0.09569 (13)0.54181 (13)0.0243 (4)
H10B0.1209−0.11900.60280.029*
C11B0.07368 (19)−0.12675 (13)0.49744 (13)0.0267 (4)
H11B0.0164−0.16950.52760.032*
C12B0.10036 (19)−0.09221 (13)0.40720 (13)0.0252 (4)
C13B0.18152 (18)−0.02639 (12)0.35903 (12)0.0234 (3)
H13B0.1974−0.00470.29820.028*
C14B0.23843 (17)0.00630 (12)0.40353 (12)0.0216 (3)
H14B0.29040.05220.37240.026*
C15B0.47645 (17)0.22221 (12)0.41892 (12)0.0199 (3)
H15B0.51910.18670.38740.024*
C16B0.33609 (17)0.25916 (11)0.39207 (11)0.0190 (3)
C17B0.29910 (19)0.26082 (12)0.31672 (12)0.0235 (4)
H17B0.36070.23790.28320.028*
C18B0.17122 (19)0.29640 (12)0.29164 (12)0.0238 (4)
H18B0.14870.29760.24100.029*
C19B0.07559 (17)0.33051 (12)0.34104 (12)0.0206 (3)
C20B0.11367 (18)0.32937 (13)0.41542 (12)0.0236 (4)
H20B0.05210.35230.44900.028*
C21B0.24170 (18)0.29470 (13)0.44049 (12)0.0230 (3)
H21B0.26480.29520.49020.028*
C22B−0.06331 (17)0.36802 (12)0.31357 (12)0.0226 (3)
H22C−0.12090.37260.36280.027*
H22D−0.09550.32630.29990.027*
C23B−0.07409 (18)0.46057 (12)0.23353 (12)0.0222 (3)
H23B−0.02040.45460.18300.027*
C24B−0.21841 (19)0.49194 (14)0.21189 (14)0.0283 (4)
H24D−0.22490.54960.16190.042*
H24E−0.27310.49620.26150.042*
H24F−0.24810.44970.19860.042*
C25B−0.02021 (19)0.52833 (13)0.25018 (13)0.0261 (4)
H25D−0.03150.58600.20050.039*
H25E0.07260.50940.25860.039*
H25F−0.06780.53210.30190.039*
C26B0.55916 (19)0.29752 (13)0.39370 (13)0.0259 (4)
H26D0.64770.27200.41060.039*
H26E0.51870.33370.42350.039*
H26F0.56280.33410.33130.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0317 (2)0.0282 (2)0.0251 (2)−0.00099 (19)−0.00806 (19)−0.0156 (2)
O1A0.0279 (7)0.0444 (9)0.0403 (9)−0.0088 (7)0.0044 (7)−0.0188 (8)
O2A0.0319 (7)0.0213 (6)0.0328 (8)−0.0038 (6)−0.0056 (6)−0.0101 (6)
O3A0.0293 (7)0.0294 (8)0.0534 (10)−0.0063 (6)−0.0183 (7)−0.0113 (7)
N1A0.0240 (7)0.0240 (8)0.0242 (8)−0.0025 (6)−0.0026 (6)−0.0104 (7)
N2A0.0237 (7)0.0205 (7)0.0192 (7)−0.0059 (6)−0.0021 (6)−0.0085 (6)
N3A0.0242 (7)0.0228 (7)0.0204 (7)−0.0082 (6)0.0006 (6)−0.0108 (6)
N4A0.0207 (7)0.0215 (7)0.0179 (7)−0.0060 (6)0.0000 (5)−0.0096 (6)
N5A0.0204 (7)0.0215 (7)0.0207 (7)−0.0044 (6)0.0000 (6)−0.0089 (6)
N6A0.0233 (7)0.0216 (7)0.0225 (8)−0.0067 (6)−0.0038 (6)−0.0031 (6)
C1A0.0236 (9)0.0387 (11)0.0324 (11)−0.0002 (8)−0.0019 (8)−0.0214 (9)
C2A0.0245 (9)0.0480 (13)0.0381 (12)0.0005 (9)−0.0016 (8)−0.0252 (11)
C3A0.0263 (9)0.0316 (10)0.0369 (11)−0.0060 (8)−0.0009 (8)−0.0162 (9)
C4A0.0260 (9)0.0228 (9)0.0274 (10)−0.0034 (7)−0.0023 (7)−0.0103 (8)
C5A0.0261 (9)0.0208 (8)0.0221 (9)−0.0023 (7)−0.0035 (7)−0.0067 (7)
C6A0.0222 (8)0.0194 (8)0.0170 (8)−0.0052 (7)−0.0015 (6)−0.0059 (7)
C7A0.0211 (8)0.0222 (8)0.0185 (8)−0.0086 (7)0.0036 (6)−0.0101 (7)
C8A0.0242 (8)0.0251 (9)0.0199 (8)−0.0063 (7)−0.0010 (7)−0.0102 (7)
C9A0.0219 (8)0.0225 (8)0.0181 (8)−0.0078 (7)0.0013 (6)−0.0085 (7)
C10A0.0235 (8)0.0260 (9)0.0213 (9)−0.0050 (7)−0.0042 (7)−0.0118 (7)
C11A0.0229 (8)0.0223 (8)0.0212 (8)−0.0063 (7)−0.0006 (7)−0.0102 (7)
C12A0.0210 (8)0.0211 (8)0.0211 (8)−0.0077 (7)−0.0006 (7)−0.0063 (7)
C13A0.0276 (9)0.0281 (9)0.0236 (9)−0.0084 (8)−0.0056 (7)−0.0108 (8)
C14A0.0278 (9)0.0271 (9)0.0217 (9)−0.0081 (7)−0.0019 (7)−0.0127 (8)
C15A0.0188 (7)0.0277 (9)0.0237 (9)−0.0064 (7)0.0001 (7)−0.0156 (8)
C16A0.0202 (8)0.0257 (9)0.0232 (9)−0.0044 (7)−0.0017 (7)−0.0158 (7)
C17A0.0161 (7)0.0379 (10)0.0291 (10)−0.0031 (7)−0.0017 (7)−0.0229 (9)
C18A0.0223 (8)0.0303 (9)0.0271 (9)0.0031 (7)−0.0087 (7)−0.0169 (8)
C19A0.0253 (8)0.0270 (9)0.0219 (9)−0.0046 (7)−0.0033 (7)−0.0135 (8)
C20A0.0200 (8)0.0302 (9)0.0249 (9)−0.0032 (7)0.0005 (7)−0.0156 (8)
C21A0.0194 (8)0.0235 (8)0.0253 (9)0.0006 (7)−0.0024 (7)−0.0128 (7)
C22A0.0358 (10)0.0306 (10)0.0243 (10)−0.0064 (9)−0.0033 (8)−0.0103 (8)
C23A0.0316 (10)0.0495 (13)0.0220 (10)−0.0044 (10)−0.0032 (8)−0.0151 (9)
C24A0.0591 (16)0.0597 (17)0.0254 (12)−0.0043 (14)−0.0077 (11)−0.0072 (11)
C25A0.0485 (13)0.0537 (15)0.0329 (12)−0.0124 (12)0.0026 (10)−0.0271 (11)
C26A0.0302 (9)0.0316 (10)0.0365 (11)−0.0084 (8)0.0002 (8)−0.0218 (9)
S1B0.0269 (2)0.0210 (2)0.0219 (2)−0.00602 (17)0.00018 (17)−0.00583 (18)
O1B0.0294 (7)0.0398 (9)0.0595 (11)0.0027 (7)−0.0061 (7)−0.0330 (8)
O2B0.0632 (12)0.0635 (12)0.0423 (10)−0.0376 (10)−0.0172 (9)−0.0123 (9)
O3B0.0617 (11)0.0308 (8)0.0368 (9)−0.0003 (8)−0.0182 (8)−0.0170 (7)
N1B0.0223 (7)0.0268 (8)0.0259 (8)−0.0030 (6)−0.0033 (6)−0.0143 (7)
N2B0.0200 (7)0.0225 (7)0.0187 (7)−0.0027 (6)−0.0006 (6)−0.0097 (6)
N3B0.0208 (7)0.0199 (7)0.0230 (8)−0.0015 (6)−0.0017 (6)−0.0102 (6)
N4B0.0186 (6)0.0204 (7)0.0169 (7)−0.0041 (6)−0.0004 (5)−0.0084 (6)
N5B0.0189 (6)0.0196 (7)0.0206 (7)−0.0023 (6)−0.0041 (6)−0.0090 (6)
N6B0.0496 (11)0.0242 (8)0.0289 (9)−0.0095 (8)−0.0165 (8)−0.0060 (7)
C1B0.0246 (9)0.0281 (9)0.0293 (10)−0.0051 (8)−0.0015 (7)−0.0153 (8)
C2B0.0279 (10)0.0427 (12)0.0428 (13)−0.0046 (9)0.0005 (9)−0.0278 (11)
C3B0.0344 (11)0.0352 (11)0.0511 (14)−0.0029 (9)−0.0021 (10)−0.0296 (11)
C4B0.0318 (10)0.0255 (9)0.0338 (11)−0.0052 (8)−0.0006 (8)−0.0170 (8)
C5B0.0228 (8)0.0274 (9)0.0228 (9)−0.0019 (7)−0.0051 (7)−0.0125 (8)
C6B0.0168 (7)0.0232 (8)0.0194 (8)−0.0033 (6)0.0013 (6)−0.0097 (7)
C7B0.0157 (7)0.0190 (8)0.0216 (8)−0.0017 (6)0.0005 (6)−0.0106 (7)
C8B0.0201 (8)0.0239 (8)0.0195 (8)−0.0032 (7)−0.0005 (6)−0.0102 (7)
C9B0.0173 (7)0.0190 (8)0.0219 (8)−0.0016 (6)−0.0030 (6)−0.0086 (7)
C10B0.0243 (8)0.0241 (9)0.0205 (9)−0.0064 (7)−0.0035 (7)−0.0047 (7)
C11B0.0289 (9)0.0215 (9)0.0265 (10)−0.0083 (7)−0.0076 (8)−0.0042 (7)
C12B0.0280 (9)0.0224 (9)0.0259 (9)−0.0040 (7)−0.0087 (7)−0.0089 (7)
C13B0.0260 (8)0.0226 (8)0.0199 (8)−0.0029 (7)−0.0030 (7)−0.0079 (7)
C14B0.0191 (8)0.0207 (8)0.0223 (9)−0.0037 (7)−0.0011 (7)−0.0071 (7)
C15B0.0205 (8)0.0181 (8)0.0206 (8)−0.0029 (6)0.0006 (6)−0.0090 (7)
C16B0.0219 (8)0.0155 (7)0.0192 (8)−0.0046 (6)0.0007 (6)−0.0074 (6)
C17B0.0281 (9)0.0229 (8)0.0201 (9)−0.0012 (7)−0.0001 (7)−0.0118 (7)
C18B0.0296 (9)0.0233 (9)0.0209 (9)−0.0024 (7)−0.0052 (7)−0.0112 (7)
C19B0.0220 (8)0.0169 (8)0.0210 (8)−0.0054 (6)−0.0014 (7)−0.0058 (7)
C20B0.0229 (8)0.0258 (9)0.0226 (9)−0.0019 (7)0.0006 (7)−0.0124 (7)
C21B0.0240 (8)0.0264 (9)0.0214 (9)−0.0022 (7)−0.0013 (7)−0.0138 (7)
C22B0.0213 (8)0.0240 (8)0.0225 (9)−0.0070 (7)−0.0022 (7)−0.0086 (7)
C23B0.0224 (8)0.0233 (8)0.0195 (8)−0.0014 (7)−0.0008 (7)−0.0092 (7)
C24B0.0260 (9)0.0302 (10)0.0289 (10)0.0015 (8)−0.0071 (8)−0.0137 (8)
C25B0.0250 (9)0.0228 (9)0.0286 (10)−0.0035 (7)−0.0003 (7)−0.0105 (8)
C26B0.0237 (8)0.0232 (9)0.0289 (10)−0.0068 (7)−0.0003 (7)−0.0091 (8)
Geometric parameters (Å, º) top
S1A—C6A1.6747 (17)S1B—C6B1.6777 (19)
O1A—C3A1.423 (3)O1B—C3B1.422 (3)
O1A—C2A1.424 (3)O1B—C2B1.428 (3)
O2A—N6A1.225 (2)O2B—N6B1.224 (3)
O3A—N6A1.228 (2)O3B—N6B1.234 (2)
N1A—C5A1.439 (2)N1B—C5B1.439 (2)
N1A—C1A1.464 (2)N1B—C1B1.470 (2)
N1A—C4A1.467 (2)N1B—C4B1.470 (3)
N2A—C6A1.352 (2)N2B—C6B1.352 (2)
N2A—N3A1.3836 (19)N2B—N3B1.385 (2)
N2A—C5A1.467 (2)N2B—C5B1.480 (2)
N3A—C7A1.297 (2)N3B—C7B1.303 (2)
N4A—N5A1.384 (2)N4B—C7B1.383 (2)
N4A—C7A1.389 (2)N4B—C6B1.390 (2)
N4A—C6A1.391 (2)N4B—N5B1.3939 (18)
N5A—C8A1.280 (2)N5B—C8B1.279 (2)
N6A—C12A1.469 (2)N6B—C12B1.467 (2)
C1A—C2A1.519 (3)C1B—C2B1.512 (3)
C1A—H1AA0.9700C1B—H1BA0.9700
C1A—H1AB0.9700C1B—H1BB0.9700
C2A—H2AA0.9700C2B—H2BA0.9700
C2A—H2AB0.9700C2B—H2BB0.9700
C3A—C4A1.508 (3)C3B—C4B1.509 (3)
C3A—H3AA0.9700C3B—H3BA0.9700
C3A—H3AB0.9700C3B—H3BB0.9700
C4A—H4AA0.9700C4B—H4BA0.9700
C4A—H4AB0.9700C4B—H4BB0.9700
C5A—H5AA0.9700C5B—H5BA0.9700
C5A—H5AB0.9700C5B—H5BB0.9700
C7A—C15A1.497 (2)C7B—C15B1.502 (2)
C8A—C9A1.466 (3)C8B—C9B1.469 (2)
C8A—H8AA0.9300C8B—H8BA0.9300
C9A—C10A1.401 (2)C9B—C14B1.396 (2)
C9A—C14A1.401 (2)C9B—C10B1.398 (2)
C10A—C11A1.383 (3)C10B—C11B1.390 (2)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.384 (2)C11B—C12B1.380 (3)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.385 (2)C12B—C13B1.385 (3)
C13A—C14A1.384 (3)C13B—C14B1.384 (2)
C13A—H13A0.9300C13B—H13B0.9300
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.521 (3)C15B—C16B1.517 (2)
C15A—C26A1.536 (2)C15B—C26B1.533 (2)
C15A—H15A0.9800C15B—H15B0.9800
C16A—C17A1.391 (3)C16B—C21B1.394 (2)
C16A—C21A1.402 (2)C16B—C17B1.400 (2)
C17A—C18A1.385 (3)C17B—C18B1.388 (3)
C17A—H17A0.9300C17B—H17B0.9300
C18A—C19A1.397 (3)C18B—C19B1.398 (2)
C18A—H18A0.9300C18B—H18B0.9300
C19A—C20A1.393 (3)C19B—C20B1.393 (2)
C19A—C22A1.504 (3)C19B—C22B1.507 (2)
C20A—C21A1.389 (3)C20B—C21B1.388 (3)
C20A—H20A0.9300C20B—H20B0.9300
C21A—H21A0.9300C21B—H21B0.9300
C22A—C23A1.539 (3)C22B—C23B1.539 (3)
C22A—H22A0.9700C22B—H22C0.9700
C22A—H22B0.9700C22B—H22D0.9700
C23A—C25A1.517 (3)C23B—C24B1.525 (3)
C23A—C24A1.525 (3)C23B—C25B1.526 (2)
C23A—H23A0.9800C23B—H23B0.9800
C24A—H24A0.9600C24B—H24D0.9600
C24A—H24B0.9600C24B—H24E0.9600
C24A—H24C0.9600C24B—H24F0.9600
C25A—H25A0.9600C25B—H25D0.9600
C25A—H25B0.9600C25B—H25E0.9600
C25A—H25C0.9600C25B—H25F0.9600
C26A—H26A0.9600C26B—H26D0.9600
C26A—H26B0.9600C26B—H26E0.9600
C26A—H26C0.9600C26B—H26F0.9600
C3A—O1A—C2A109.53 (17)C3B—O1B—C2B109.47 (17)
C5A—N1A—C1A113.59 (15)C5B—N1B—C1B113.34 (14)
C5A—N1A—C4A114.12 (14)C5B—N1B—C4B113.71 (15)
C1A—N1A—C4A110.92 (16)C1B—N1B—C4B110.06 (15)
C6A—N2A—N3A113.39 (14)C6B—N2B—N3B113.63 (14)
C6A—N2A—C5A127.05 (14)C6B—N2B—C5B124.40 (15)
N3A—N2A—C5A118.50 (14)N3B—N2B—C5B120.99 (14)
C7A—N3A—N2A104.86 (14)C7B—N3B—N2B104.62 (14)
N5A—N4A—C7A118.58 (14)C7B—N4B—C6B108.92 (14)
N5A—N4A—C6A133.08 (14)C7B—N4B—N5B120.03 (14)
C7A—N4A—C6A108.27 (14)C6B—N4B—N5B131.03 (14)
C8A—N5A—N4A119.42 (15)C8B—N5B—N4B116.47 (14)
O2A—N6A—O3A123.82 (16)O2B—N6B—O3B124.42 (18)
O2A—N6A—C12A118.39 (15)O2B—N6B—C12B117.97 (18)
O3A—N6A—C12A117.78 (15)O3B—N6B—C12B117.60 (18)
N1A—C1A—C2A108.67 (16)N1B—C1B—C2B110.51 (15)
N1A—C1A—H1AA110.0N1B—C1B—H1BA109.5
C2A—C1A—H1AA110.0C2B—C1B—H1BA109.5
N1A—C1A—H1AB110.0N1B—C1B—H1BB109.5
C2A—C1A—H1AB110.0C2B—C1B—H1BB109.5
H1AA—C1A—H1AB108.3H1BA—C1B—H1BB108.1
O1A—C2A—C1A111.07 (17)O1B—C2B—C1B111.46 (18)
O1A—C2A—H2AA109.4O1B—C2B—H2BA109.3
C1A—C2A—H2AA109.4C1B—C2B—H2BA109.3
O1A—C2A—H2AB109.4O1B—C2B—H2BB109.3
C1A—C2A—H2AB109.4C1B—C2B—H2BB109.3
H2AA—C2A—H2AB108.0H2BA—C2B—H2BB108.0
O1A—C3A—C4A111.35 (16)O1B—C3B—C4B111.32 (16)
O1A—C3A—H3AA109.4O1B—C3B—H3BA109.4
C4A—C3A—H3AA109.4C4B—C3B—H3BA109.4
O1A—C3A—H3AB109.4O1B—C3B—H3BB109.4
C4A—C3A—H3AB109.4C4B—C3B—H3BB109.4
H3AA—C3A—H3AB108.0H3BA—C3B—H3BB108.0
N1A—C4A—C3A109.15 (15)N1B—C4B—C3B108.88 (17)
N1A—C4A—H4AA109.8N1B—C4B—H4BA109.9
C3A—C4A—H4AA109.8C3B—C4B—H4BA109.9
N1A—C4A—H4AB109.8N1B—C4B—H4BB109.9
C3A—C4A—H4AB109.8C3B—C4B—H4BB109.9
H4AA—C4A—H4AB108.3H4BA—C4B—H4BB108.3
N1A—C5A—N2A116.59 (15)N1B—C5B—N2B114.58 (15)
N1A—C5A—H5AA108.1N1B—C5B—H5BA108.6
N2A—C5A—H5AA108.1N2B—C5B—H5BA108.6
N1A—C5A—H5AB108.1N1B—C5B—H5BB108.6
N2A—C5A—H5AB108.1N2B—C5B—H5BB108.6
H5AA—C5A—H5AB107.3H5BA—C5B—H5BB107.6
N2A—C6A—N4A102.74 (14)N2B—C6B—N4B102.29 (15)
N2A—C6A—S1A126.88 (14)N2B—C6B—S1B128.04 (14)
N4A—C6A—S1A130.37 (13)N4B—C6B—S1B129.42 (13)
N3A—C7A—N4A110.73 (15)N3B—C7B—N4B110.39 (15)
N3A—C7A—C15A125.90 (15)N3B—C7B—C15B126.41 (15)
N4A—C7A—C15A123.37 (16)N4B—C7B—C15B123.18 (14)
N5A—C8A—C9A119.57 (16)N5B—C8B—C9B119.14 (16)
N5A—C8A—H8AA120.2N5B—C8B—H8BA120.4
C9A—C8A—H8AA120.2C9B—C8B—H8BA120.4
C10A—C9A—C14A119.39 (17)C14B—C9B—C10B120.12 (16)
C10A—C9A—C8A118.07 (15)C14B—C9B—C8B121.56 (16)
C14A—C9A—C8A122.52 (15)C10B—C9B—C8B118.32 (16)
C11A—C10A—C9A120.99 (16)C11B—C10B—C9B120.24 (17)
C11A—C10A—H10A119.5C11B—C10B—H10B119.9
C9A—C10A—H10A119.5C9B—C10B—H10B119.9
C10A—C11A—C12A117.79 (16)C12B—C11B—C10B118.00 (17)
C10A—C11A—H11A121.1C12B—C11B—H11B121.0
C12A—C11A—H11A121.1C10B—C11B—H11B121.0
C11A—C12A—C13A123.17 (17)C11B—C12B—C13B123.11 (16)
C11A—C12A—N6A118.50 (15)C11B—C12B—N6B118.55 (17)
C13A—C12A—N6A118.33 (16)C13B—C12B—N6B118.34 (17)
C14A—C13A—C12A118.34 (16)C14B—C13B—C12B118.41 (17)
C14A—C13A—H13A120.8C14B—C13B—H13B120.8
C12A—C13A—H13A120.8C12B—C13B—H13B120.8
C13A—C14A—C9A120.31 (16)C13B—C14B—C9B120.03 (16)
C13A—C14A—H14A119.8C13B—C14B—H14B120.0
C9A—C14A—H14A119.8C9B—C14B—H14B120.0
C7A—C15A—C16A111.00 (14)C7B—C15B—C16B110.80 (14)
C7A—C15A—C26A110.41 (16)C7B—C15B—C26B110.48 (14)
C16A—C15A—C26A111.16 (14)C16B—C15B—C26B111.55 (15)
C7A—C15A—H15A108.0C7B—C15B—H15B108.0
C16A—C15A—H15A108.0C16B—C15B—H15B108.0
C26A—C15A—H15A108.0C26B—C15B—H15B108.0
C17A—C16A—C21A118.34 (18)C21B—C16B—C17B118.29 (16)
C17A—C16A—C15A120.76 (16)C21B—C16B—C15B120.76 (15)
C21A—C16A—C15A120.87 (16)C17B—C16B—C15B120.92 (15)
C18A—C17A—C16A120.63 (16)C18B—C17B—C16B120.54 (16)
C18A—C17A—H17A119.7C18B—C17B—H17B119.7
C16A—C17A—H17A119.7C16B—C17B—H17B119.7
C17A—C18A—C19A121.48 (18)C17B—C18B—C19B121.29 (16)
C17A—C18A—H18A119.3C17B—C18B—H18B119.4
C19A—C18A—H18A119.3C19B—C18B—H18B119.4
C20A—C19A—C18A117.81 (18)C20B—C19B—C18B117.76 (16)
C20A—C19A—C22A121.42 (17)C20B—C19B—C22B121.53 (16)
C18A—C19A—C22A120.74 (18)C18B—C19B—C22B120.70 (16)
C21A—C20A—C19A121.09 (16)C21B—C20B—C19B121.32 (16)
C21A—C20A—H20A119.5C21B—C20B—H20B119.3
C19A—C20A—H20A119.5C19B—C20B—H20B119.3
C20A—C21A—C16A120.65 (17)C20B—C21B—C16B120.78 (16)
C20A—C21A—H21A119.7C20B—C21B—H21B119.6
C16A—C21A—H21A119.7C16B—C21B—H21B119.6
C19A—C22A—C23A112.74 (17)C19B—C22B—C23B114.17 (14)
C19A—C22A—H22A109.0C19B—C22B—H22C108.7
C23A—C22A—H22A109.0C23B—C22B—H22C108.7
C19A—C22A—H22B109.0C19B—C22B—H22D108.7
C23A—C22A—H22B109.0C23B—C22B—H22D108.7
H22A—C22A—H22B107.8H22C—C22B—H22D107.6
C25A—C23A—C24A111.04 (19)C24B—C23B—C25B111.29 (15)
C25A—C23A—C22A111.87 (18)C24B—C23B—C22B109.62 (15)
C24A—C23A—C22A110.0 (2)C25B—C23B—C22B110.98 (15)
C25A—C23A—H23A107.9C24B—C23B—H23B108.3
C24A—C23A—H23A107.9C25B—C23B—H23B108.3
C22A—C23A—H23A107.9C22B—C23B—H23B108.3
C23A—C24A—H24A109.5C23B—C24B—H24D109.5
C23A—C24A—H24B109.5C23B—C24B—H24E109.5
H24A—C24A—H24B109.5H24D—C24B—H24E109.5
C23A—C24A—H24C109.5C23B—C24B—H24F109.5
H24A—C24A—H24C109.5H24D—C24B—H24F109.5
H24B—C24A—H24C109.5H24E—C24B—H24F109.5
C23A—C25A—H25A109.5C23B—C25B—H25D109.5
C23A—C25A—H25B109.5C23B—C25B—H25E109.5
H25A—C25A—H25B109.5H25D—C25B—H25E109.5
C23A—C25A—H25C109.5C23B—C25B—H25F109.5
H25A—C25A—H25C109.5H25D—C25B—H25F109.5
H25B—C25A—H25C109.5H25E—C25B—H25F109.5
C15A—C26A—H26A109.5C15B—C26B—H26D109.5
C15A—C26A—H26B109.5C15B—C26B—H26E109.5
H26A—C26A—H26B109.5H26D—C26B—H26E109.5
C15A—C26A—H26C109.5C15B—C26B—H26F109.5
H26A—C26A—H26C109.5H26D—C26B—H26F109.5
H26B—C26A—H26C109.5H26E—C26B—H26F109.5
C6A—N2A—N3A—C7A1.26 (19)C6B—N2B—N3B—C7B0.14 (19)
C5A—N2A—N3A—C7A170.29 (15)C5B—N2B—N3B—C7B−169.00 (15)
C7A—N4A—N5A—C8A−178.80 (16)C7B—N4B—N5B—C8B−154.02 (16)
C6A—N4A—N5A—C8A4.7 (3)C6B—N4B—N5B—C8B27.8 (2)
C5A—N1A—C1A—C2A−173.33 (17)C5B—N1B—C1B—C2B176.37 (17)
C4A—N1A—C1A—C2A56.5 (2)C4B—N1B—C1B—C2B−55.0 (2)
C3A—O1A—C2A—C1A60.5 (2)C3B—O1B—C2B—C1B−58.5 (2)
N1A—C1A—C2A—O1A−58.7 (2)N1B—C1B—C2B—O1B56.2 (2)
C2A—O1A—C3A—C4A−60.2 (2)C2B—O1B—C3B—C4B61.0 (2)
C5A—N1A—C4A—C3A173.79 (16)C5B—N1B—C4B—C3B−175.09 (15)
C1A—N1A—C4A—C3A−56.4 (2)C1B—N1B—C4B—C3B56.5 (2)
O1A—C3A—C4A—N1A58.0 (2)O1B—C3B—C4B—N1B−60.3 (2)
C1A—N1A—C5A—N2A−58.7 (2)C1B—N1B—C5B—N2B52.5 (2)
C4A—N1A—C5A—N2A69.8 (2)C4B—N1B—C5B—N2B−74.16 (19)
C6A—N2A—C5A—N1A−98.3 (2)C6B—N2B—C5B—N1B−90.8 (2)
N3A—N2A—C5A—N1A94.32 (18)N3B—N2B—C5B—N1B77.1 (2)
N3A—N2A—C6A—N4A−1.32 (19)N3B—N2B—C6B—N4B−2.46 (18)
C5A—N2A—C6A—N4A−169.22 (16)C5B—N2B—C6B—N4B166.25 (15)
N3A—N2A—C6A—S1A177.59 (13)N3B—N2B—C6B—S1B172.11 (12)
C5A—N2A—C6A—S1A9.7 (3)C5B—N2B—C6B—S1B−19.2 (2)
N5A—N4A—C6A—N2A177.62 (17)C7B—N4B—C6B—N2B3.77 (17)
C7A—N4A—C6A—N2A0.86 (18)N5B—N4B—C6B—N2B−177.93 (15)
N5A—N4A—C6A—S1A−1.2 (3)C7B—N4B—C6B—S1B−170.69 (13)
C7A—N4A—C6A—S1A−177.99 (14)N5B—N4B—C6B—S1B7.6 (3)
N2A—N3A—C7A—N4A−0.63 (19)N2B—N3B—C7B—N4B2.35 (18)
N2A—N3A—C7A—C15A179.58 (16)N2B—N3B—C7B—C15B−178.88 (15)
N5A—N4A—C7A—N3A−177.44 (14)C6B—N4B—C7B—N3B−4.03 (19)
C6A—N4A—C7A—N3A−0.1 (2)N5B—N4B—C7B—N3B177.45 (14)
N5A—N4A—C7A—C15A2.3 (2)C6B—N4B—C7B—C15B177.16 (15)
C6A—N4A—C7A—C15A179.64 (16)N5B—N4B—C7B—C15B−1.4 (2)
N4A—N5A—C8A—C9A179.47 (15)N4B—N5B—C8B—C9B179.34 (14)
N5A—C8A—C9A—C10A−179.63 (17)N5B—C8B—C9B—C14B−8.0 (3)
N5A—C8A—C9A—C14A−1.0 (3)N5B—C8B—C9B—C10B172.27 (17)
C14A—C9A—C10A—C11A−0.4 (3)C14B—C9B—C10B—C11B0.6 (3)
C8A—C9A—C10A—C11A178.28 (17)C8B—C9B—C10B—C11B−179.69 (17)
C9A—C10A—C11A—C12A1.0 (3)C9B—C10B—C11B—C12B1.8 (3)
C10A—C11A—C12A—C13A−0.7 (3)C10B—C11B—C12B—C13B−2.1 (3)
C10A—C11A—C12A—N6A179.12 (16)C10B—C11B—C12B—N6B178.35 (18)
O2A—N6A—C12A—C11A21.0 (2)O2B—N6B—C12B—C11B27.0 (3)
O3A—N6A—C12A—C11A−158.05 (18)O3B—N6B—C12B—C11B−152.71 (19)
O2A—N6A—C12A—C13A−159.17 (17)O2B—N6B—C12B—C13B−152.5 (2)
O3A—N6A—C12A—C13A21.8 (3)O3B—N6B—C12B—C13B27.8 (3)
C11A—C12A—C13A—C14A−0.2 (3)C11B—C12B—C13B—C14B0.0 (3)
N6A—C12A—C13A—C14A179.95 (16)N6B—C12B—C13B—C14B179.46 (17)
C12A—C13A—C14A—C9A0.8 (3)C12B—C13B—C14B—C9B2.5 (3)
C10A—C9A—C14A—C13A−0.5 (3)C10B—C9B—C14B—C13B−2.8 (3)
C8A—C9A—C14A—C13A−179.18 (17)C8B—C9B—C14B—C13B177.46 (16)
N3A—C7A—C15A—C16A−99.4 (2)N3B—C7B—C15B—C16B−113.39 (18)
N4A—C7A—C15A—C16A80.9 (2)N4B—C7B—C15B—C16B65.2 (2)
N3A—C7A—C15A—C26A24.4 (2)N3B—C7B—C15B—C26B10.8 (2)
N4A—C7A—C15A—C26A−155.41 (16)N4B—C7B—C15B—C26B−170.62 (15)
C7A—C15A—C16A—C17A−122.66 (17)C7B—C15B—C16B—C21B47.1 (2)
C26A—C15A—C16A—C17A114.03 (18)C26B—C15B—C16B—C21B−76.4 (2)
C7A—C15A—C16A—C21A59.1 (2)C7B—C15B—C16B—C17B−134.77 (17)
C26A—C15A—C16A—C21A−64.3 (2)C26B—C15B—C16B—C17B101.69 (19)
C21A—C16A—C17A—C18A0.6 (2)C21B—C16B—C17B—C18B−0.5 (3)
C15A—C16A—C17A—C18A−177.77 (15)C15B—C16B—C17B—C18B−178.69 (17)
C16A—C17A—C18A—C19A0.3 (3)C16B—C17B—C18B—C19B−0.7 (3)
C17A—C18A—C19A—C20A−1.0 (3)C17B—C18B—C19B—C20B1.3 (3)
C17A—C18A—C19A—C22A177.05 (16)C17B—C18B—C19B—C22B−179.32 (17)
C18A—C19A—C20A—C21A0.9 (3)C18B—C19B—C20B—C21B−0.7 (3)
C22A—C19A—C20A—C21A−177.15 (16)C22B—C19B—C20B—C21B179.96 (17)
C19A—C20A—C21A—C16A−0.1 (3)C19B—C20B—C21B—C16B−0.5 (3)
C17A—C16A—C21A—C20A−0.7 (2)C17B—C16B—C21B—C20B1.1 (3)
C15A—C16A—C21A—C20A177.66 (15)C15B—C16B—C21B—C20B179.32 (17)
C20A—C19A—C22A—C23A102.2 (2)C20B—C19B—C22B—C23B105.08 (19)
C18A—C19A—C22A—C23A−75.7 (2)C18B—C19B—C22B—C23B−74.2 (2)
C19A—C22A—C23A—C25A−60.2 (2)C19B—C22B—C23B—C24B−179.82 (14)
C19A—C22A—C23A—C24A175.88 (19)C19B—C22B—C23B—C25B−56.47 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4A—H4AB···O3Ai0.972.533.450 (3)157
C5A—H5AB···O3Bii0.972.563.221 (3)126
C8A—H8AA···S1A0.932.433.186 (2)138
C13A—H13A···O3Aiii0.932.433.064 (3)125
C13B—H13B···N1Aiv0.932.553.332 (2)141
C15A—H15A···O1Av0.982.273.212 (2)161
C5B—H5BA···S1B0.972.833.252 (2)107
C8B—H8BA···S1B0.932.553.1823 (19)125
C22B—H22D···S1Aiv0.972.863.801 (2)163
N6A—O2A···Cg1i1.23 (1)3.00 (1)3.6928 (19)115 (1)
C11A—H11A···Cg2i0.932.523.405 (2)158
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x+1, y, z+1; (iii) −x, −y+1, −z+2; (iv) x−1, y, z−1; (v) x−1, y, z.

Experimental details

Crystal data
Chemical formulaC26H32N6O3S
Mr508.65
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)10.3104 (1), 16.9650 (2), 17.1863 (2)
α, β, γ (°)62.656 (1), 79.907 (1), 78.307 (1)
V (Å3)2603.16 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.16
Crystal size (mm)0.44 × 0.25 × 0.15
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.931, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections		50102, 15162, 11421
Rint0.044
(sin θ/λ)max (Å−1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.161, 1.05
No. of reflections15162
No. of parameters655
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.23, −0.55

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4A—H4AB···O3Ai0.972.533.450 (3)157
C5A—H5AB···O3Bii0.972.563.221 (3)126
C8A—H8AA···S1A0.932.433.186 (2)138
C13A—H13A···O3Aiii0.932.433.064 (3)125
C13B—H13B···N1Aiv0.932.553.332 (2)141
C15A—H15A···O1Av0.982.273.212 (2)161
C8B—H8BA···S1B0.932.553.1823 (19)125
C22B—H22D···S1Aiv0.972.863.801 (2)163
N6A—O2A···Cg1i1.225 (2)3.0012 (17)3.6928 (19)115.19 (12)
C11A—H11A···Cg2i0.932.523.405 (2)158
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x+1, y, z+1; (iii) −x, −y+1, −z+2; (iv) x−1, y, z−1; (v) x−1, y, z.
 

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

KVS and BK are grateful to Kerala State Council for Science, Technology and the Environment, Thiruvanan­thapuram, for financial assistance. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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ISSN: 2056-9890
Volume 65| Part 3| March 2009| Pages o495-o496
doi:10.1107/S1600536809003870
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